3-Aminophenol → 1-(3-(2-Fluoropropan-2-yl)isoxazol-5-yl)-3-(3-hydroxyphenyl)urea

HRID 1917727노트

반응식

HRID 1917727 반응식
[F:1][C:2]([C:5]1[CH:9]=[C:8]([NH:10][C:11](=[O:19])OC2C=CC=CC=2)[O:7][N:6]=1)([CH3:4])[CH3:3].[NH2:20][C:21]1[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=1.CN(C1C=CC=CN=1)C>C1COCC1>[F:1][C:2]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=2)=[O:19])[O:7][N:6]=1)([CH3:3])[CH3:4]

참가 물질

5

반응물 3

HCID 115683-AminophenolHCID 218852-DimethylaminopyridineHCID 66876626Phenyl 3-(2-fluoropropan-2-yl)isoxazol-5-ylcarbamate

생성물 1

HCID 668757701-(3-(2-Fluoropropan-2-yl)isoxazol-5-yl)-3-(3-hydroxyphenyl)urea수율 74%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To THF (10 mL) was added phenyl 3-(2-fluoropropan-2-yl)isoxazol-5-ylcarbamate from the previous step (500 mg, 1.9 mmol), 3-aminophenol (207 mg, 1.9 mmol) and dimethylaminopyridine (60 mg, 0.5 mmol) and the mixture stirred overnight at room temperature. The mixture was concentrated in vacuo and purified by chromatography on silica gel (10-50% EtOAc/hexanes) to afford 1-(3-(2-fluoropropan-2-yl)isoxazol-5-yl)-3-(3-hydroxyphenyl)urea (390 mg, 1.4 mmol, 74%). LC-MS (ESI) m/z 280 (M+H)+.

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by chromatography on silica gel (10-50% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-ae15f05d79d14012966f779a1b1a747b
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618289B2

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